Five Questions Every Mentor Must Ask

One of my partners, Mats Lederhausen, recently shared with me a mentorship framework, first inspired by wellness guru, Deepak Chopra, that he’s evolved and used over the years. The framework is an amazingly simple-yet-powerful set of five critical questions. As venture capitalists and advisors, we spend significant time partnering with portfolio companies and very often find ourselves in a mentoring role. These five questions, when asked in the order presented, form an effective diagnostic tool that can provide better guidance to mentees, employees, or generally anyone with whom you are playing the role of a counselor. Additionally, they can serve as a self-diagnosis of one’s own capabilities and opportunities.

Here are the questions:

1. What is it that you really want to be and do? 2. What are you doing really well that is helping you get there? 3. What are you not doing well that is preventing you from getting there? 4. What will you do differently tomorrow to meet those challenges? 5. How can I help / where do you need the most help?

Let’s briefly look at each question:

1. What is it that you really want to be and do? This question is about aspiration and purpose. The reason why someone is doing what they are doing should come out here. The question is also meant to get at the business goals and broader aspirations of an individual – someone wishing to be successful in business so that they can do more to help others, for example. The answer to question one should surface the driving passion of individuals – what is it they do or wish they could be great at doing?

2. What are you doing really well that is helping you get there? This question helps spotlight a core strength and the person’s ability to execute towards his/her goal. What is someone naturally good at doing? Detailed and standardized operations? Leading and motivating staff? Numbers? What is it that someone does better than the average person that can help her achieve her aspiration?

3. What are you not doing well that is preventing you from getting there? This is about facilitating an honest and critical assessment of the roadblocks, challenges or weaknesses in a person or company that is slowing their ability to win the game; to meet the goal from question one.

4. What will you do different tomorrow to meet those challenges? Questions two and three help determine whether people are spending the right time on the right things. Progress cannot be measured just by hard work. Someone may have a great work ethic, but if he is not focused on the right priorities, then “you’re making good time, but you’re lost,” as another one of my partners likes to say. People also have a tendency to practice and repeat what they are already good at doing. It is human nature to show off your best side and hide weaknesses. As a kid playing racquet sports, I remember being asked once why I kept practicing my forehand when my backhand sucked. Use this question to probe whether the person has the aptitude to change behavior. Will the person practice start practicing his backhand?

5. How can I help / where do you need the most help? The answers to the first four questions matched against areas where you as a mentor have particular strengths, relationships, or learning resources – should help determine how you can best help someone achieve the goal.

These questions will help you assess where you can really help an individual or a company. Try these five critical questions the next time you are interviewing a mentee candidate, the next time you have a mentoring session, or answer them yourself as a self-diagnostic. The answers can help you or your mentees put together a sensible game plan for forward progress.